Reaction Steps
The N-phenylmethyl-3,9,10,11-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-amine (45.3 mg) and palladium on charcoal (10% w/w; 2.3 mg) in ethyl acetate (3 mL) in a steel autoclave was stirred under hydrogen (2 bar) for 2.5 hours. The mixture was then passed through a plug of alumina and concentrated in vacuo to afford a green oil. Column chromatography, eluting with chloroform-methanol 49:1), afforded the title compound as a pale orange gum (8.6 mg, 24%); High Resolution Mass Spectrometry Found: M+Na+ 354.1319 (C18H21NO5Na requires 354.1317); νmax/cm−1 (thin film) 3364, 2946, 2850, 1599, 1572; NMR Spectrum δH (400 MHz, CDCl3) 3.65 (3H, s, OCH3), 3.88-3.90 (1H, m, 5-H or 7-H), 3.91 (3H, s, OCH3), 3.92 (3H, s, OCH3), 3.95 (3H, s, OCH3), 3.95-3.98 (1H, m, 5-H or 7-H), 4.37 (1H, d, J 11.5 Hz, 5-H or 7-H), 4.70 (1H, d, J 11.5 Hz, 5-H or 7-H), 6.74 (1H, s, 8-H), 6.88 (1H, d, J 8.3 Hz, 2-H or 1-H), 6.94 (1H; d, J 8.3 Hz, 1-H or 2-H); NMR Spectrum δC (100 MHz, CDCl3) 56.04, 56.31, 56.74, 56.85, 62.53, 71.48, 107.05, 114.42, 114.68, 118.32, 128.60, 129.76, 130.46, 131.96, 132.58, 146.78, 147.42, 147.53; m/z (ES) 331 (M, 100%); Rf (chloroform-methanol 49:1) 0.18.
